N-Triflyl Phosphoric Triamide (N-TPT) as an Efficient Activator for ‘On-Water’ Accelerated Aquacatalytic Polar Substrate Allylation

Abstract

The development of sustainable, functional-group-tolerant catalysis is highly significant from the perspectives of safety, user-friendliness, and cost-effectiveness. We report herein the triple hydrogen-bonding donor activator N-triflyl phosphoric triamide ( N-TPT) for the synergistic Brønsted acid aquacatalysis of multicomponent allylation ‘on-water’. The reaction demonstrated remarkable efficiency in converting polar diol substrate, such as 1,3-dihydroxyacetone, into α-tertiary amine derivative incorporating homoallylic amine functionalities using bulk water as the reaction medium. The single crystal X-ray structure and control experiments highlighted the crucial role of multiple hydrogen bonds in enabling this aqueous reaction.

Key words

aquacatalysis - organocatalysis - Brønsted acid - allylboration - α-tertiary amines - ‘on-water’ chemistry

Publication History

Received: 19 February 2024

Accepted after revision: 12 March 2024

Accepted Manuscript online:
12 March 2024

Article published online:
02 April 2024

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